3-Bromopyridine-2,5-diamine

Base Information

• Chemical Name: 3-Bromopyridine-2,5-diamine
• CAS No.: 896160-69-3
• Molecular Formula: C5H6 Br N3
• Molecular Weight: 188.027
• Hs Code.: 29333999
• European Community (EC) Number: 687-507-6
• Mol file: 896160-69-3.mol

Synonyms:3-bromopyridine-2,5-diamine;2,5-Diamino-3-bromopyridine;896160-69-3;114292-91-0;3-Bromo-2,5-diaminopyridine;MFCD03427651;2,5-Diamino-3-bormopyridine;BASIONIC(TM)ST99;SCHEMBL913127;YJENCMIONVUOCW-UHFFFAOYSA-N;3-Bromo-2,5-diaminopyridine, 97%;AKOS005259513;AM86331;SB52559;DS-12114;CS-0042827;FT-0651934;FT-0727892;F10345;A803164;A861118;J-507279;W-200521

Chemical Property of 3-Bromopyridine-2,5-diamine

Chemical Property:

• Melting Point: 117-122°C
• Refractive Index: 1.6400 (estimate)
• PSA: 64.93000
• Density: 1.6770 (rough estimate)
• LogP: 2.17090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 186.97451
• Heavy Atom Count: 9
• Complexity: 98.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-Diamino-3-bromopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Br)N)N

Technology Process of 3-Bromopyridine-2,5-diamine

There total 2 articles about 3-Bromopyridine-2,5-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

3-bromo-5-nitro-pyridin-2-ylamine (15862-31-4) → 3-bromopyridine-2,5-diamine (896160-69-3)

Guidance literature:

With borane-ammonia complex; copper(II) oxide; In methanol; at 50 ℃; for 1h;

DOI:10.1002/cctc.201902391

Reference yield:

5-nitro-pyridin-2-ylamine (4214-76-0,67476-67-9) → 3-bromopyridine-2,5-diamine (896160-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / toluene / 1 h / 80 °C / Inert atmosphere

2: ammonium chloride; iron / water; methanol / 2 h / 80 °C

With N-Bromosuccinimide; iron; ammonium chloride; In methanol; water; toluene;

DOI:10.1016/j.bmc.2017.05.035

Reference yield: 80.0%

3-bromopyridine-2,5-diamine (896160-69-3) + 5’-O-(4,4’-dimethoxytrityl)-3’-O-(tert-butyldimethylsilyl)-1β-[1-methyl-4-(3-nitro-1,2,4-triazol-1-yl)pyrimidin-2-onyl]-1,2-dideoxy-D-ribofuranose → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-1-methyl-4-N-(6-amino-5-bromopyridin-3-yl)pseudocytidine

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 24h; Reflux;

DOI:10.1016/j.bmc.2017.05.035

upstream raw materials:

5-nitro-pyridin-2-ylamine

3-bromo-5-nitro-pyridin-2-ylamine

Downstream raw materials:

N-(6-amino-5-bromopyridin-3-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide

Refernces

• 1、 Wang, Lei,Taniguchi, Yosuke,Okamura, Hidenori,Sasaki, Shigeki. "Effect of the 3-halo substitution of the 2′-deoxy aminopyridinyl-pseudocytidine derivatives on the selectivity and stability of antiparallel triplex DNA with a CG inversion site". . p. 3853 - 3860. Retrieved 2017/06/13.